Halogen Or Unsaturation Patents (Class 562/574)
  • Patent number: 4535167
    Abstract: Chiral N-protected, N-substituted .alpha.-amino acids are described. These compounds are prepared by condensation of an N-protected .alpha.-amino acid with an aldehyde followed by the selective reductive cleavage of an oxazolidinone intermediate.
    Type: Grant
    Filed: May 23, 1983
    Date of Patent: August 13, 1985
    Assignee: Merck & Co. Inc.
    Inventor: Roger M. Freidinger
  • Patent number: 4508921
    Abstract: A process for preparing .alpha.-alkyl amino acids by enantioretentive .alpha.-alkylation of .alpha.-amino acids is described. The products are bioactive compounds including some useful as therapeutic agents.
    Type: Grant
    Filed: June 28, 1984
    Date of Patent: April 2, 1985
    Assignee: Merck & Co., Inc.
    Inventors: Joseph S. Amato, Leonard M. Weinstock, Sandor Karady
  • Patent number: 4492799
    Abstract: Novel halo-4-alkenoic acid compounds which are useful intermediates for the synthesis of insecticides and miticides.
    Type: Grant
    Filed: July 2, 1979
    Date of Patent: January 8, 1985
    Assignee: Union Carbide Corporation
    Inventor: Thomas N. Wheeler
  • Patent number: 4484003
    Abstract: .beta.-Chloroalanine is prepared by reacting in an aqueous medium an aziridine-2-carboxylate with hydrogen chloride in an amount of 2.0-5.0 moles per mole of the aziridine-2-carboxyalte and causing the thus-formed .beta.-chloroalanine to selectively crystallize out from the liquid reaction mixture. Since the solution recovered after the isolation of the crystallized .beta.-chloroalanine still contains .beta.-chloroalanine and by-produced .alpha.-chloro-.beta.-alanine dissolved therein, they may be converted into an aziridine-2-carboxylate by treating them with a base to recirculate it for reuse.
    Type: Grant
    Filed: December 29, 1982
    Date of Patent: November 20, 1984
    Assignee: Mitsui Toatsu Chemicals, Incorporated
    Inventors: Masaharu Ohoka, Toshio Katoh, Ryuichi Mita, Nobuyuki Kawashima, Chojiro Higuchi, Nobuhiro Kawashima, Akihiro Yamaguchi, Shousuke Nagai, Takao Takano
  • Patent number: 4454156
    Abstract: (R,S)- and (S)-4-amino-hepta-5,6-dienoic acid are novel inhibitors of gamma-aminobutyric acid transaminase (GABA-T).
    Type: Grant
    Filed: May 9, 1983
    Date of Patent: June 12, 1984
    Assignee: Merrell-Toraude et Compagnie
    Inventor: Patrick Casara
  • Patent number: 4436910
    Abstract: Aqueous solutions of sodium salts of .alpha.-aminocarboxylic acids practically free of foreign salts are produced by saponifying the corresponding hydantoin at a temperature between 110.degree. C. and 180.degree. C. with a mixture, in each case based on the hydantoin, of 1 equivalent of sodium hydroxide and 2 equivalents of calcium oxide or hydroxide, separating off the precipitated calcium carbonate after the end of the saponification and concentrating the aqueous sodium salt solution remaining to drive off the ammonia contained therein.
    Type: Grant
    Filed: February 10, 1982
    Date of Patent: March 13, 1984
    Assignee: Degussa Aktiengesellschaft
    Inventors: Axel Kleemann, Bernd Lehmann, Jurgen Martens
  • Patent number: 4431817
    Abstract: Novel 1-fluoromethyl-substituted alkyl amines are disclosed. The novel compounds have biological activity including decarboxylase inhibition.
    Type: Grant
    Filed: April 14, 1980
    Date of Patent: February 14, 1984
    Assignee: Merck & Co., Inc.
    Inventors: Arthur A. Patchett, Janos Kollonitsch
  • Patent number: 4418077
    Abstract: Fluorinated aminobutyric acid and diaminobutane compounds in vivo are inhibitors of gamma-aminobutyric acid transaminase and have the following formula: ##STR1## wherein: Y represents hydrogen or fluorine;Z represents --CH.sub.2 NR.sub.1 R.sub.2, where R.sub.1 and R.sub.2 are as defined below, or --COR.sub.3 where R.sub.3 is as defined below;R.sub.a represents hydrogen or R.sub.4, where R.sub.4 is as defined below;R.sub.1 represents hydrogen, C.sub.1 -C.sub.6 alkyl or phenyl-(C.sub.1 -C.sub.4 alkyl);R.sub.2 represents hydrogen, C.sub.1 -C.sub.6 alkyl, phenyl-(C.sub.1 -C.sub.4 alkyl) or, when R.sub.a is hydrogen, R.sub.4, where R.sub.4 is as defined below;R.sub.3 represents hydroxy, or when R.sub.a is hydrogen, C.sub.1 -C.sub.8 alkoxy, --NR.sub.5 R.sub.6, where R.sub.5 and R.sub.6 are as defined below, or an aminocarboxylic acid residue derived by removal of an hydrogen atom from the amino moiety of an L-aminocarboxylic acid;each R.sub.4, independently, represents C.sub.2 -C.sub.
    Type: Grant
    Filed: August 21, 1981
    Date of Patent: November 29, 1983
    Assignee: Merrell Toraude et Compagnie
    Inventors: Philippe Bey, Fritz Gerhart, Michel Jung, Daniel Schirlin
  • Patent number: 4386103
    Abstract: Dichloroamino acid derivatives other than .alpha.-dichloroamino acids are prepared from chlorination of corresponding amino acids, and are found to be potent germicidal and fungicidal agents.
    Type: Grant
    Filed: January 30, 1981
    Date of Patent: May 31, 1983
    Assignee: Merck & Co., Inc.
    Inventors: Stefano A. Pogany, Takeru Higuchi
  • Patent number: 4351954
    Abstract: Halogenated .alpha.-amino acids as new compounds are obtained by subjecting halogenated ethanes and an ester of acrylic acid or crotonic acid to addition reaction, adding sodium azide to the adducts, reducing the resultant mixtures with hydrogen and subsequently hydrolyzing the reduction products.
    Type: Grant
    Filed: August 3, 1981
    Date of Patent: September 28, 1982
    Assignees: Agency of Industrial Science & Technology, Ministry of International Trade & Industry
    Inventors: Hiroshige Muramatsu, Teruo Ueda
  • Patent number: 4326071
    Abstract: Novel compounds of the following general formula are useful pharmacological agents: ##STR1## wherein Y is FCH.sub.2 - or F.sub.2 CH-; R.sub.1 is hydroxy, a straight or branched alkoxy group of from 1 to 8 carbon atoms, -NR.sub.10 R.sub.11 wherein each of R.sub.10 and R.sub.11 is hydrogen or a straight or branched alkyl group of from 1 to 4 carbon atoms or ##STR2## wherein R.sub.12 is hydrogen, a straight or branched lower alkyl group of from 1 to 4 carbon atoms, benzyl or p-hydroxybenzyl; R.sub.2 is hydrogen, alkylcarbonyl wherein the alkyl moiety has from 1 to 4 carbon atoms and is straight or branched, alkoxycarbonyl wherein the alkoxy moiety has from 1 to 4 carbon atoms and is straight or branched or ##STR3## wherein R.sub.8 is hydrogen, a straight or branched lower alkyl group of from 1 to 4 carbon atoms, benzyl or p-hydroxybenzyl; and n is the integer 2 or 3; pharmaceutically acceptable salts and individual optical isomers thereof.
    Type: Grant
    Filed: September 28, 1977
    Date of Patent: April 20, 1982
    Assignee: Merrell Toraude et Compagnie
    Inventors: Philippe Bey, Michel Jung
  • Patent number: 4301186
    Abstract: This invention relates to new ammonium salts of .alpha.-ketocarboxylic acids, to their use for the production of amines in situ by photochemical decomposition and to photochemically hardenable coating compositions containing these ammonium salts.
    Type: Grant
    Filed: June 28, 1979
    Date of Patent: November 17, 1981
    Assignee: Bayer Aktiengesellschaft
    Inventors: Wolfram Mayer, Hans Rudolph, Eckhard De Cleur, Manfred Schonfelder
  • Patent number: 4283554
    Abstract: A novel production process of .beta.-chloroalanine from chloroacetaldehyde is provided. In this process, a bisulfite or sulfite addition compound of chloroacetaldehyde is first reacted, in an aqueous solution, with ammonia and, then, reacted with hydrocyanic acid or a salt thereof. Thus, .alpha.-amino-.beta.-chloropropionitrile is formed. This .alpha.-amino-.beta.-chloropropionitrile is hydrolyzed under an acidic condition to form .beta.-chloroalanine.
    Type: Grant
    Filed: May 29, 1980
    Date of Patent: August 11, 1981
    Assignee: Showa Denko Kabushiki Kaisha
    Inventors: Chozo Inoue, Soyao Moriguchi
  • Patent number: 4264590
    Abstract: It has been found that dipeptides containing a 3-halo-D-alanine C-terminus are powerful antibacterials and produce a highly useful synergistic effect with antibiotics.
    Type: Grant
    Filed: June 9, 1980
    Date of Patent: April 28, 1981
    Assignee: Abbott Laboratories
    Inventors: Daniel I. Chu, Jerry R. Martin, Alford M. Thomas, Norman E. Wideburg
  • Patent number: 4254284
    Abstract: Novel compounds of the following general formula are useful in the preparation of 4-aminohex-5-enoic acid and 4-aminohex-5-ynoic acid which are useful pharmacological agents: ##STR1## wherein R.sub.1 is hydroxy, amino, or tert-butoxy.
    Type: Grant
    Filed: January 14, 1980
    Date of Patent: March 3, 1981
    Assignee: Merrell Toraude et Compagnie
    Inventors: Maurice W. Gittos, Gerard J. Letertre
  • Patent number: 4248677
    Abstract: This invention relates to a process for producing alpha-aminocarboxylic acids and salts thereof. More specifically, this invention relates to a process for producing alpha-aminocarboxylic acids or salts thereof from organic imine compounds by electrochemical reduction.
    Type: Grant
    Filed: July 10, 1979
    Date of Patent: February 3, 1981
    Assignee: Tokuyama Soda Kabushiki Kaisha
    Inventor: Shozo Kato
  • Patent number: 4239916
    Abstract: New catalysts for isocyanurate foams are those comprising aminomethacrylate salts. The foams are obtained by the polymerization of an aromatic polyisocyanate, and a polyether or polyester polyol in the presence of a blowing agent and said amino methacrylate salts falling within the following structural formula: ##STR1## where the radicals represented by R are hydroxy lower alkyl, and M is selected from the group consisting of sodium, potassium, cesium, lithium and rubidium. The novel foams are useful in preparing rigid, flexible, semi-rigid, or semi-flexible materials such as panels, slabs or sprayed foam surfaces.
    Type: Grant
    Filed: October 30, 1978
    Date of Patent: December 16, 1980
    Assignee: Texaco Development Corp.
    Inventors: Robert L. Zimmerman, Edward E. McEntire, Howard P. Klein
  • Patent number: 4228102
    Abstract: What is disclosed is a method for making amides of the formula ##STR1## wherein R.sub.1 is hydrogen or methyl,R.sub.3 is straight-chain or branched alkyl or unsubstituted or substituted aryl, andR.sub.4 is hydrogen or straight-chain or branched unsubstituted or substituted alkyl, which comprises reacting an ester of the formula ##STR2## wherein R.sub.2 is alkyl having 1 to 6 carbon atoms, with heating and under autogenous pressure, in a homogeneous phase, with an amine of the formula ##STR3## said amine being present in an amount which is stoichiometrically deficient up to an amount which is in small stoichiometric excess with respect to said ester.
    Type: Grant
    Filed: February 23, 1979
    Date of Patent: October 14, 1980
    Assignee: Rohm GmbH
    Inventors: Siegmund Besecke, Wolfgang Gaenzler, Guenter Schroeder
  • Patent number: 4219660
    Abstract: There are disclosed herein derivatives of bisfunctionalized compounds, wherein said compounds have been formed by the introduction of a nitro group and a hydroxyl group in the form of an ester into a conjugated diene molecule by treatment of said conjugated dienes with nitric acid in the presence of a carboxylic acid anhydride. The novel compounds produced by this process are useful as bactericides, fungicides and valuable organic synthesis intermediates.
    Type: Grant
    Filed: June 24, 1977
    Date of Patent: August 26, 1980
    Assignee: Hoffmann-La Roche Inc.
    Inventor: Pius A. Wehrli
  • Patent number: 4178463
    Abstract: Novel compounds of the following general formula are useful in the preparation of 4-aminohex-5-enoic acid and 4-aminohex-5-ynoic acid which are useful pharmacological agents: ##STR1## wherein R.sub.1 is hydroxy, amino, or tert-butoxy.
    Type: Grant
    Filed: January 30, 1978
    Date of Patent: December 11, 1979
    Assignee: Merrell Toraude et Compagnie
    Inventors: Maurice W. Gittos, Gerard J. Letertre
  • Patent number: 4160777
    Abstract: Textiles, particularly carpets, are endowed with oil and water repellency and soil resistance by treatment thereof with certain detergent-compatible fluorochemmical compounds which can also be used in conjunction with anionic or nonionic detergents to provide cleaning/treating compositions for cleaning such textiles simultaneously with the treatment. The textile treating compositions of the invention comprise certain detergent-compatible fluorochemical compounds which are dissolved and/or dispersed in a suitable liquid vehicle. The textile treating/cleaning compositions of the invention also contain an anionic and/or a nonionic detergent.
    Type: Grant
    Filed: January 14, 1977
    Date of Patent: July 10, 1979
    Assignee: Minnesota Mining and Manufacturing Company
    Inventor: Basil L. Loudas
  • Patent number: 4149012
    Abstract: The racemate of 3-fluoro-alanine, and salts thereof, are prepared by reductive amination of 3-fluoro-pyruvic acid, its hydrate, or salts thereof, via the intermediate 2-imino-3-fluoro propionic acid salt, using alkali metal borohydrides as reducing agents. The racemates thus obtained are valuable in the production of 3-fluoro-D-alanine and its pharmacologically acceptable salts, and derivatives thereof, which are potent antibacterial agents.
    Type: Grant
    Filed: October 7, 1977
    Date of Patent: April 10, 1979
    Assignee: Merck & Co., Inc.
    Inventors: Ulf-H. Dolling, Edward J. J. Grabowski, Erwin F. Schoenewaldt, Meyer Sletzinger
  • Patent number: RE31980
    Abstract: Novel compounds of the following general formula are useful pharmacologic agents: ##STR1## R is .[.selected from.]. hydrogen.[., alkylcarbonyl wherein the alkyl moiety contains from 1 to 4 carbon atoms, alkoxycarbonyl wherein the alkoxy moiety contains from 1 to 4 carbon atoms and may be straight or branched, and ##STR2## wherein R.sub.10 is selected from hydrogen, a straight or branched lower alkyl group of from 1 to 4 carbon atoms, benzyl and p-hydroxybenzyl.].; R.sub.2 is .[.selected from.]. hydroxy.[., a straight or branched alkoxy group of from 1 to 8 carbon atoms, a lower alkylamino group wherein the alkyl moiety contains from 1 to 4 carbon atoms, and ##STR3## wherein R.sub.4 is selected from hydrogen, a straight or branched lower alkyl group of from 1 to 4 carbon atoms, benzyl, and p-hydroxybenzyl.].; R.sub.3 is .[.selected from.]. hydrogen.[., chlorine, bromine, and iodine.].; [A] is .[.selected from.]. ##STR4## .[.and --CH.dbd.CH--.]. wherein R.sub.1 is .[.selected from.]. hydrogen.[.
    Type: Grant
    Filed: January 14, 1983
    Date of Patent: September 3, 1985
    Assignee: Merrell Toraude et Compagnie
    Inventors: Brian W. Metcalf, Michel Jung